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#$Date: 2024-04-11 23:20:00 +0300 (Thu, 11 Apr 2024) $
#$Revision: 291189 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/90/4039027.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4039027
loop_
_publ_author_name
'Garsi, Jean-Baptiste'
'Aguiar, Pedro M.'
'Berger, Gilles'
'Maris, Thierry'
'Hanessian, Stephen'
_publ_section_title
;
 Pseudodiproline (Pro-Cyp) Oligomers Fold into Helical Polyproline Type
 secondary structures
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4283
_journal_page_last               4293
_journal_paper_doi               10.1021/acs.joc.3c02840
_journal_volume                  89
_journal_year                    2024
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C28 H46 N2 O7'
_chemical_formula_sum            'C28 H46 N2 O7'
_chemical_formula_weight         522.67
_chemical_name_systematic
;
tert-Butyl (S)-2-((S)-hydroxy((1R,2R)-2-((S)-2-((S)-hydroxy-
((1R,2R)-2-(methoxycarbonyl)cyclopentyl)methyl)pyrrolidine-1-
carbonyl)cyclopentyl)methyl)pyrrolidine-1-carboxylate
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'I 2y'
_space_group_name_H-M_alt        'I 1 2 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2021-06-15
_audit_creation_method
;
FinalCif V85 by Daniel Kratzert, Freiburg 2021,
https://github.com/dkratzert/FinalCif
;
_cell_angle_alpha                90
_cell_angle_beta                 100.471(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.8992(4)
_cell_length_b                   6.1645(2)
_cell_length_c                   35.2338(11)
_cell_measurement_reflns_used    4801
_cell_measurement_temperature    100
_cell_measurement_theta_max      70.053
_cell_measurement_theta_min      2.550
_cell_volume                     2755.03(15)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection
;
APEX 3 (2019) Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 8.3
_diffrn_detector_type            'Bruker APEX2 CCD'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker Smart APEX'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_collimation    'Focusing mirrors'
_diffrn_radiation_monochromator  'Quazar MX Mirror Optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0384
_diffrn_reflns_av_unetI/netI     0.0353
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_number            18561
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.176
_diffrn_reflns_theta_min         2.550
_diffrn_source                   'Microfocus Source'
_diffrn_source_current           0.65
_diffrn_source_power             0.02912
_diffrn_source_target            Cu
_diffrn_source_type              'Incoatec I\mS High Brilliance Microsource'
_diffrn_source_voltage           44.8
_exptl_absorpt_coefficient_mu    0.729
_exptl_absorpt_correction_T_max  0.4027
_exptl_absorpt_correction_T_min  0.2893
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1618 before and 0.0517 after correction.
The Ratio of minimum to maximum transmission is 0.7184.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.260
_exptl_crystal_description       block
_exptl_crystal_F_000             1136
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.186
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.00(18)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     347
_refine_ls_number_reflns         4899
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0360
_refine_ls_R_factor_gt           0.0328
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0514P)²+0.2943P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0808
_refine_ls_wR_factor_ref         0.0831
_reflns_Friedel_coverage         0.693
_reflns_Friedel_fraction_full    0.853
_reflns_Friedel_fraction_max     0.846
_reflns_number_gt                4588
_reflns_number_total             4899
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            han588.cif
_cod_data_source_block           han588
_cod_database_code               4039027
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y, -z'
3 'x+1/2, y+1/2, z+1/2'
4 '-x+1/2, y+1/2, -z+1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.53899(11) 0.8021(3) 0.10771(4) 0.0264(3) Uani 1 1 d . . . . .
O2 O 0.42060(11) 0.5681(3) 0.12599(4) 0.0298(3) Uani 1 1 d . . . . .
O3 O 0.40184(11) 0.5314(3) 0.20085(4) 0.0265(3) Uani 1 1 d . . . . .
H3 H 0.401(2) 0.532(6) 0.1764(9) 0.042(8) Uiso 1 1 d . . . . .
O4 O 0.59235(10) 0.5111(3) 0.31162(4) 0.0240(3) Uani 1 1 d . . . . .
O5 O 0.67118(11) 0.5557(3) 0.38672(4) 0.0266(3) Uani 1 1 d . . . . .
H5 H 0.659(2) 0.540(6) 0.3626(9) 0.039(7) Uiso 1 1 d . . . . .
O6 O 0.65311(12) 0.3702(3) 0.50072(4) 0.0291(3) Uani 1 1 d . . . . .
O7 O 0.62446(15) 0.6970(3) 0.52409(4) 0.0374(4) Uani 1 1 d . . . . .
N1 N 0.58515(13) 0.6079(3) 0.16140(5) 0.0239(4) Uani 1 1 d . . . . .
N2 N 0.44591(13) 0.5304(3) 0.33806(4) 0.0229(3) Uani 1 1 d . . . . .
C1 C 0.50811(16) 0.6533(4) 0.13102(6) 0.0240(4) Uani 1 1 d . . . . .
C2 C 0.46276(16) 0.8925(4) 0.07512(5) 0.0259(4) Uani 1 1 d . . . . .
C3 C 0.37554(17) 1.0087(4) 0.09066(6) 0.0317(5) Uani 1 1 d . . . . .
H3A H 0.334741 0.903051 0.102655 0.048 Uiso 1 1 calc R U . . .
H3B H 0.329046 1.081984 0.069432 0.048 Uiso 1 1 calc R U . . .
H3C H 0.406518 1.116069 0.109936 0.048 Uiso 1 1 calc R U . . .
C4 C 0.42248(18) 0.7148(4) 0.04629(6) 0.0321(5) Uani 1 1 d . . . . .
H4A H 0.482421 0.636589 0.039283 0.048 Uiso 1 1 calc R U . . .
H4B H 0.380411 0.779619 0.023109 0.048 Uiso 1 1 calc R U . . .
H4C H 0.378645 0.613516 0.057892 0.048 Uiso 1 1 calc R U . . .
C5 C 0.53021(18) 1.0531(4) 0.05817(6) 0.0352(5) Uani 1 1 d . . . . .
H5A H 0.559920 1.158794 0.077958 0.053 Uiso 1 1 calc R U . . .
H5B H 0.486912 1.128713 0.036433 0.053 Uiso 1 1 calc R U . . .
H5C H 0.587549 0.975945 0.049126 0.053 Uiso 1 1 calc R U . . .
C6 C 0.69558(16) 0.6777(4) 0.16475(6) 0.0269(4) Uani 1 1 d . . . . .
H6A H 0.712962 0.794789 0.184095 0.032 Uiso 1 1 calc R U . . .
H6B H 0.710501 0.728432 0.139634 0.032 Uiso 1 1 calc R U . . .
C7 C 0.75594(17) 0.4713(4) 0.17780(6) 0.0309(5) Uani 1 1 d . . . . .
H7A H 0.828310 0.504225 0.191420 0.037 Uiso 1 1 calc R U . . .
H7B H 0.759799 0.374780 0.155641 0.037 Uiso 1 1 calc R U . . .
C8 C 0.69017(17) 0.3689(4) 0.20513(6) 0.0282(4) Uani 1 1 d . . . . .
H8A H 0.708412 0.432968 0.231255 0.034 Uiso 1 1 calc R U . . .
H8B H 0.701909 0.210226 0.207047 0.034 Uiso 1 1 calc R U . . .
C9 C 0.57478(16) 0.4202(4) 0.18682(5) 0.0244(4) Uani 1 1 d . . . . .
H9 H 0.543229 0.294315 0.170885 0.029 Uiso 1 1 calc R U . . .
C10 C 0.50775(15) 0.4744(3) 0.21732(5) 0.0228(4) Uani 1 1 d . . . . .
H10 H 0.540754 0.601418 0.232567 0.027 Uiso 1 1 calc R U . . .
C11 C 0.50424(16) 0.2856(4) 0.24536(5) 0.0230(4) Uani 1 1 d . . . . .
H11 H 0.577729 0.252805 0.258780 0.028 Uiso 1 1 calc R U . . .
C12 C 0.45398(17) 0.0764(4) 0.22699(6) 0.0273(4) Uani 1 1 d . . . . .
H12A H 0.503798 -0.004638 0.213973 0.033 Uiso 1 1 calc R U . . .
H12B H 0.389167 0.108011 0.208035 0.033 Uiso 1 1 calc R U . . .
C13 C 0.42846(18) -0.0513(4) 0.26155(6) 0.0290(4) Uani 1 1 d . . . . .
H13A H 0.491781 -0.127613 0.275339 0.035 Uiso 1 1 calc R U . . .
H13B H 0.372137 -0.159150 0.253065 0.035 Uiso 1 1 calc R U . . .
C14 C 0.39151(17) 0.1217(4) 0.28746(6) 0.0274(4) Uani 1 1 d . . . . .
H14A H 0.418417 0.089054 0.314998 0.033 Uiso 1 1 calc R U . . .
H14B H 0.313545 0.127028 0.283222 0.033 Uiso 1 1 calc R U . . .
C15 C 0.43670(15) 0.3414(3) 0.27599(5) 0.0218(4) Uani 1 1 d . . . . .
H15 H 0.376292 0.433455 0.263427 0.026 Uiso 1 1 calc R U . . .
C16 C 0.49784(15) 0.4670(3) 0.30996(5) 0.0210(4) Uani 1 1 d . . . . .
C17 C 0.33123(15) 0.5069(4) 0.33682(5) 0.0261(4) Uani 1 1 d . . . . .
H17A H 0.316093 0.390446 0.354371 0.031 Uiso 1 1 calc R U . . .
H17B H 0.293685 0.475308 0.310320 0.031 Uiso 1 1 calc R U . . .
C18 C 0.30056(15) 0.7279(4) 0.35036(6) 0.0251(4) Uani 1 1 d . . . . .
H18A H 0.234411 0.719650 0.360798 0.030 Uiso 1 1 calc R U . . .
H18B H 0.291849 0.835193 0.329114 0.030 Uiso 1 1 calc R U . . .
C19 C 0.39398(16) 0.7850(4) 0.38185(5) 0.0256(4) Uani 1 1 d . . . . .
H19A H 0.386763 0.715987 0.406608 0.031 Uiso 1 1 calc R U . . .
H19B H 0.399368 0.944014 0.385629 0.031 Uiso 1 1 calc R U . . .
C20 C 0.49162(15) 0.6963(4) 0.36727(5) 0.0215(4) Uani 1 1 d . . . . .
H20 H 0.523280 0.815674 0.353910 0.026 Uiso 1 1 calc R U . . .
C21 C 0.57596(15) 0.6066(3) 0.39992(5) 0.0213(4) Uani 1 1 d . . . . .
H21 H 0.548207 0.470638 0.409902 0.026 Uiso 1 1 calc R U . . .
C22 C 0.60318(15) 0.7673(3) 0.43358(5) 0.0223(4) Uani 1 1 d . . . . .
H22 H 0.539254 0.789924 0.445453 0.027 Uiso 1 1 calc R U . . .
C23 C 0.64345(16) 0.9906(4) 0.42240(6) 0.0271(4) Uani 1 1 d . . . . .
H23A H 0.629612 1.008916 0.394015 0.033 Uiso 1 1 calc R U . . .
H23B H 0.608061 1.109367 0.434016 0.033 Uiso 1 1 calc R U . . .
C24 C 0.76213(17) 0.9919(4) 0.43820(6) 0.0301(4) Uani 1 1 d . . . . .
H24A H 0.801627 0.919677 0.420148 0.036 Uiso 1 1 calc R U . . .
H24B H 0.788826 1.141805 0.443055 0.036 Uiso 1 1 calc R U . . .
C25 C 0.77079(16) 0.8648(4) 0.47576(6) 0.0281(4) Uani 1 1 d . . . . .
H25A H 0.749586 0.955180 0.496287 0.034 Uiso 1 1 calc R U . . .
H25B H 0.843675 0.812229 0.484655 0.034 Uiso 1 1 calc R U . . .
C26 C 0.69424(15) 0.6743(4) 0.46508(5) 0.0234(4) Uani 1 1 d . . . . .
H26 H 0.731036 0.555318 0.453511 0.028 Uiso 1 1 calc R U . . .
C27 C 0.65370(15) 0.5874(4) 0.49973(5) 0.0243(4) Uani 1 1 d . . . . .
C28 C 0.61638(18) 0.2728(4) 0.53326(6) 0.0318(5) Uani 1 1 d . . . . .
H28A H 0.611083 0.115259 0.529646 0.048 Uiso 1 1 calc R U . . .
H28B H 0.546931 0.331770 0.535107 0.048 Uiso 1 1 calc R U . . .
H28C H 0.666277 0.305320 0.557033 0.048 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C1 O1 C2 120.29(16) . .
C10 O3 H3 104(2) . .
C21 O5 H5 110(2) . .
C27 O6 C28 116.07(17) . .
C1 N1 C6 124.40(17) . .
C1 N1 C9 120.36(17) . .
C6 N1 C9 111.80(17) . .
C16 N2 C17 125.25(16) . .
C16 N2 C20 121.13(16) . .
C17 N2 C20 110.76(15) . .
O1 C1 N1 111.69(17) . .
O2 C1 O1 124.91(19) . .
O2 C1 N1 123.40(19) . .
O1 C2 C3 109.25(16) . .
O1 C2 C4 110.24(19) . .
O1 C2 C5 101.80(16) . .
C3 C2 C4 113.31(18) . .
C5 C2 C3 110.6(2) . .
C5 C2 C4 111.07(18) . .
C2 C3 H3A 109.5 . .
C2 C3 H3B 109.5 . .
C2 C3 H3C 109.5 . .
H3A C3 H3B 109.5 . .
H3A C3 H3C 109.5 . .
H3B C3 H3C 109.5 . .
C2 C4 H4A 109.5 . .
C2 C4 H4B 109.5 . .
C2 C4 H4C 109.5 . .
H4A C4 H4B 109.5 . .
H4A C4 H4C 109.5 . .
H4B C4 H4C 109.5 . .
C2 C5 H5A 109.5 . .
C2 C5 H5B 109.5 . .
C2 C5 H5C 109.5 . .
H5A C5 H5B 109.5 . .
H5A C5 H5C 109.5 . .
H5B C5 H5C 109.5 . .
N1 C6 H6A 111.3 . .
N1 C6 H6B 111.3 . .
N1 C6 C7 102.41(18) . .
H6A C6 H6B 109.2 . .
C7 C6 H6A 111.3 . .
C7 C6 H6B 111.3 . .
C6 C7 H7A 111.2 . .
C6 C7 H7B 111.2 . .
C6 C7 C8 102.93(17) . .
H7A C7 H7B 109.1 . .
C8 C7 H7A 111.2 . .
C8 C7 H7B 111.2 . .
C7 C8 H8A 110.8 . .
C7 C8 H8B 110.8 . .
C7 C8 C9 104.77(16) . .
H8A C8 H8B 108.9 . .
C9 C8 H8A 110.8 . .
C9 C8 H8B 110.8 . .
N1 C9 C8 103.08(16) . .
N1 C9 H9 109.8 . .
N1 C9 C10 112.16(17) . .
C8 C9 H9 109.8 . .
C10 C9 C8 112.04(15) . .
C10 C9 H9 109.8 . .
O3 C10 C9 112.87(15) . .
O3 C10 H10 107.9 . .
O3 C10 C11 108.10(16) . .
C9 C10 H10 107.9 . .
C11 C10 C9 111.90(17) . .
C11 C10 H10 107.9 . .
C10 C11 H11 108.8 . .
C10 C11 C12 115.24(16) . .
C10 C11 C15 111.59(17) . .
C12 C11 H11 108.8 . .
C12 C11 C15 103.50(16) . .
C15 C11 H11 108.8 . .
C11 C12 H12A 111.1 . .
C11 C12 H12B 111.1 . .
C11 C12 C13 103.39(16) . .
H12A C12 H12B 109.0 . .
C13 C12 H12A 111.1 . .
C13 C12 H12B 111.1 . .
C12 C13 H13A 110.9 . .
C12 C13 H13B 110.9 . .
C12 C13 C14 104.47(17) . .
H13A C13 H13B 108.9 . .
C14 C13 H13A 110.9 . .
C14 C13 H13B 110.9 . .
C13 C14 H14A 110.5 . .
C13 C14 H14B 110.5 . .
C13 C14 C15 106.19(16) . .
H14A C14 H14B 108.7 . .
C15 C14 H14A 110.5 . .
C15 C14 H14B 110.5 . .
C11 C15 C14 105.85(16) . .
C11 C15 H15 108.1 . .
C14 C15 H15 108.1 . .
C16 C15 C11 112.69(16) . .
C16 C15 C14 113.84(15) . .
C16 C15 H15 108.1 . .
O4 C16 N2 121.11(17) . .
O4 C16 C15 120.91(17) . .
N2 C16 C15 117.97(16) . .
N2 C17 H17A 111.2 . .
N2 C17 H17B 111.2 . .
N2 C17 C18 102.67(17) . .
H17A C17 H17B 109.1 . .
C18 C17 H17A 111.2 . .
C18 C17 H17B 111.2 . .
C17 C18 H18A 111.2 . .
C17 C18 H18B 111.2 . .
C17 C18 C19 102.67(16) . .
H18A C18 H18B 109.1 . .
C19 C18 H18A 111.2 . .
C19 C18 H18B 111.2 . .
C18 C19 H19A 110.7 . .
C18 C19 H19B 110.7 . .
C18 C19 C20 105.12(16) . .
H19A C19 H19B 108.8 . .
C20 C19 H19A 110.7 . .
C20 C19 H19B 110.7 . .
N2 C20 C19 103.18(15) . .
N2 C20 H20 108.9 . .
N2 C20 C21 114.01(17) . .
C19 C20 H20 108.9 . .
C21 C20 C19 112.83(15) . .
C21 C20 H20 108.9 . .
O5 C21 C20 111.73(15) . .
O5 C21 H21 108.4 . .
O5 C21 C22 107.71(15) . .
C20 C21 H21 108.4 . .
C20 C21 C22 112.19(16) . .
C22 C21 H21 108.4 . .
C21 C22 H22 108.8 . .
C21 C22 C23 114.67(15) . .
C21 C22 C26 110.31(16) . .
C23 C22 H22 108.8 . .
C23 C22 C26 105.19(16) . .
C26 C22 H22 108.8 . .
C22 C23 H23A 110.6 . .
C22 C23 H23B 110.6 . .
H23A C23 H23B 108.7 . .
C24 C23 C22 105.79(17) . .
C24 C23 H23A 110.6 . .
C24 C23 H23B 110.6 . .
C23 C24 H24A 111.2 . .
C23 C24 H24B 111.2 . .
H24A C24 H24B 109.1 . .
C25 C24 C23 102.91(17) . .
C25 C24 H24A 111.2 . .
C25 C24 H24B 111.2 . .
C24 C25 H25A 111.0 . .
C24 C25 H25B 111.0 . .
C24 C25 C26 103.76(16) . .
H25A C25 H25B 109.0 . .
C26 C25 H25A 111.0 . .
C26 C25 H25B 111.0 . .
C22 C26 H26 109.2 . .
C25 C26 C22 105.01(17) . .
C25 C26 H26 109.2 . .
C27 C26 C22 112.10(16) . .
C27 C26 C25 112.00(16) . .
C27 C26 H26 109.2 . .
O6 C27 C26 112.34(17) . .
O7 C27 O6 122.5(2) . .
O7 C27 C26 125.1(2) . .
O6 C28 H28A 109.5 . .
O6 C28 H28B 109.5 . .
O6 C28 H28C 109.5 . .
H28A C28 H28B 109.5 . .
H28A C28 H28C 109.5 . .
H28B C28 H28C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C1 1.339(3) .
O1 C2 1.478(2) .
O2 C1 1.228(3) .
O3 H3 0.86(3) .
O3 C10 1.428(2) .
O4 C16 1.240(2) .
O5 H5 0.84(3) .
O5 C21 1.425(2) .
O6 C27 1.340(3) .
O6 C28 1.448(3) .
O7 C27 1.205(3) .
N1 C1 1.351(3) .
N1 C6 1.472(3) .
N1 C9 1.484(3) .
N2 C16 1.350(2) .
N2 C17 1.479(2) .
N2 C20 1.494(3) .
C2 C3 1.517(3) .
C2 C4 1.520(3) .
C2 C5 1.511(3) .
C3 H3A 0.9800 .
C3 H3B 0.9800 .
C3 H3C 0.9800 .
C4 H4A 0.9800 .
C4 H4B 0.9800 .
C4 H4C 0.9800 .
C5 H5A 0.9800 .
C5 H5B 0.9800 .
C5 H5C 0.9800 .
C6 H6A 0.9900 .
C6 H6B 0.9900 .
C6 C7 1.519(3) .
C7 H7A 0.9900 .
C7 H7B 0.9900 .
C7 C8 1.531(3) .
C8 H8A 0.9900 .
C8 H8B 0.9900 .
C8 C9 1.544(3) .
C9 H9 1.0000 .
C9 C10 1.534(3) .
C10 H10 1.0000 .
C10 C11 1.533(3) .
C11 H11 1.0000 .
C11 C12 1.533(3) .
C11 C15 1.544(2) .
C12 H12A 0.9900 .
C12 H12B 0.9900 .
C12 C13 1.535(3) .
C13 H13A 0.9900 .
C13 H13B 0.9900 .
C13 C14 1.535(3) .
C14 H14A 0.9900 .
C14 H14B 0.9900 .
C14 C15 1.556(3) .
C15 H15 1.0000 .
C15 C16 1.520(3) .
C17 H17A 0.9900 .
C17 H17B 0.9900 .
C17 C18 1.519(3) .
C18 H18A 0.9900 .
C18 H18B 0.9900 .
C18 C19 1.524(3) .
C19 H19A 0.9900 .
C19 H19B 0.9900 .
C19 C20 1.544(2) .
C20 H20 1.0000 .
C20 C21 1.535(3) .
C21 H21 1.0000 .
C21 C22 1.536(3) .
C22 H22 1.0000 .
C22 C23 1.547(3) .
C22 C26 1.570(3) .
C23 H23A 0.9900 .
C23 H23B 0.9900 .
C23 C24 1.531(3) .
C24 H24A 0.9900 .
C24 H24B 0.9900 .
C24 C25 1.525(3) .
C25 H25A 0.9900 .
C25 H25B 0.9900 .
C25 C26 1.536(3) .
C26 H26 1.0000 .
C26 C27 1.511(3) .
C28 H28A 0.9800 .
C28 H28B 0.9800 .
C28 H28C 0.9800 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O3 H3 O2 0.86(3) 1.85(3) 2.7019(19) 169(3) . yes
O3 H3 N1 0.86(3) 2.57(3) 2.990(2) 111(2) . yes
O5 H5 O4 0.84(3) 1.85(3) 2.6710(19) 163(3) . yes
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
O3 C10 C11 C12 62.5(2) . . . .
O3 C10 C11 C15 -55.1(2) . . . .
O5 C21 C22 C23 65.2(2) . . . .
O5 C21 C22 C26 -53.3(2) . . . .
N1 C6 C7 C8 -37.3(2) . . . .
N1 C9 C10 O3 62.1(2) . . . .
N1 C9 C10 C11 -175.69(16) . . . .
N2 C17 C18 C19 -38.35(18) . . . .
N2 C20 C21 O5 71.4(2) . . . .
N2 C20 C21 C22 -167.50(15) . . . .
C1 O1 C2 C3 61.7(3) . . . .
C1 O1 C2 C4 -63.4(2) . . . .
C1 O1 C2 C5 178.62(19) . . . .
C1 N1 C6 C7 -133.5(2) . . . .
C1 N1 C9 C8 157.03(17) . . . .
C1 N1 C9 C10 -82.3(2) . . . .
C2 O1 C1 O2 6.2(3) . . . .
C2 O1 C1 N1 -173.23(18) . . . .
C6 N1 C1 O1 -11.6(3) . . . .
C6 N1 C1 O2 168.9(2) . . . .
C6 N1 C9 C8 -2.9(2) . . . .
C6 N1 C9 C10 117.77(18) . . . .
C6 C7 C8 C9 36.5(2) . . . .
C7 C8 C9 N1 -20.9(2) . . . .
C7 C8 C9 C10 -141.66(19) . . . .
C8 C9 C10 O3 177.48(18) . . . .
C8 C9 C10 C11 -60.3(2) . . . .
C9 N1 C1 O1 -168.92(17) . . . .
C9 N1 C1 O2 11.6(3) . . . .
C9 N1 C6 C7 25.5(2) . . . .
C9 C10 C11 C12 -62.4(2) . . . .
C9 C10 C11 C15 179.96(15) . . . .
C10 C11 C12 C13 -162.18(17) . . . .
C10 C11 C15 C14 151.20(16) . . . .
C10 C11 C15 C16 -83.8(2) . . . .
C11 C12 C13 C14 38.2(2) . . . .
C11 C15 C16 O4 -1.4(3) . . . .
C11 C15 C16 N2 178.10(17) . . . .
C12 C11 C15 C14 26.69(19) . . . .
C12 C11 C15 C16 151.73(16) . . . .
C12 C13 C14 C15 -21.3(2) . . . .
C13 C14 C15 C11 -3.3(2) . . . .
C13 C14 C15 C16 -127.66(18) . . . .
C14 C15 C16 O4 119.1(2) . . . .
C14 C15 C16 N2 -61.3(2) . . . .
C15 C11 C12 C13 -40.1(2) . . . .
C16 N2 C17 C18 -134.2(2) . . . .
C16 N2 C20 C19 157.86(17) . . . .
C16 N2 C20 C21 -79.4(2) . . . .
C17 N2 C16 O4 173.1(2) . . . .
C17 N2 C16 C15 -6.5(3) . . . .
C17 N2 C20 C19 -3.9(2) . . . .
C17 N2 C20 C21 118.79(18) . . . .
C17 C18 C19 C20 36.8(2) . . . .
C18 C19 C20 N2 -20.5(2) . . . .
C18 C19 C20 C21 -144.03(17) . . . .
C19 C20 C21 O5 -171.31(18) . . . .
C19 C20 C21 C22 -50.2(2) . . . .
C20 N2 C16 O4 14.0(3) . . . .
C20 N2 C16 C15 -165.49(17) . . . .
C20 N2 C17 C18 26.69(19) . . . .
C20 C21 C22 C23 -58.2(2) . . . .
C20 C21 C22 C26 -176.69(16) . . . .
C21 C22 C23 C24 -106.19(18) . . . .
C21 C22 C26 C25 134.83(16) . . . .
C21 C22 C26 C27 -103.33(19) . . . .
C22 C23 C24 C25 -35.5(2) . . . .
C22 C26 C27 O6 105.8(2) . . . .
C22 C26 C27 O7 -74.0(3) . . . .
C23 C22 C26 C25 10.66(19) . . . .
C23 C22 C26 C27 132.50(18) . . . .
C23 C24 C25 C26 42.1(2) . . . .
C24 C25 C26 C22 -32.62(19) . . . .
C24 C25 C26 C27 -154.53(17) . . . .
C25 C26 C27 O6 -136.46(18) . . . .
C25 C26 C27 O7 43.7(3) . . . .
C26 C22 C23 C24 15.17(19) . . . .
C28 O6 C27 O7 -0.8(3) . . . .
C28 O6 C27 C26 179.37(17) . . . .
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 1.00(18)
2 -0.00(18)

_cod_database_fobs_code 4039027
